1,3-bis(1-ethoxyethoxy)-5-pentylbenzene | 125265-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3-bis(1-ethoxyethoxy)-5-pentylbenzene
• 英文别名: olivetol bis(1-ethoxyethyl)ether；olivetol bis(ethoxyethyl)ether
• CAS: 125265-27-2
• 化学式: C₁₉H₃₂O₄
• 分子量: 324.461
• InChiKey: IYDUKERJYMOPIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-bis(1-ethoxyethoxy)-5-pentylbenzene 在 4-甲基苯磺酸吡啶 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 甲醇 为溶剂， 反应 1.25h， 生成 4-<2,6-dihydroxy-4-(pentyl)phenyl>-5-isopropenyl-2-fluorocyclohex-1-ene
  参考文献：
  名称：

  Halogenated cannabinoid synthesis

  摘要：

  A convenient synthesis of several tricyclic and bicyclic fluoro- and iodo analogs of cannabinoids has been reported. A new, mild methodology for the synthesis of vinyl fluorides from vinylstannanes has also been demonstrated. These C9 halo-functionalized cannabinoid analogs, along with (-) and (+)-DELTA9-THC carboxylic acids, were screened for anti-inflammatory activity in the mouse ear edema assay. It was interesting Lo find that both enantiomers of DELTA9-THC carboxylic acid were moderately active as anti-inflammatories. The bicyclic vinyl iodide (18C) also showed appreciable anti-inflammatory activity.

  DOI：

  10.1016/s0040-4020(01)90158-9
• 作为产物：
  描述：

  乙烯基乙醚 、 3,5-二羟基戊苯 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以91%的产率得到1,3-bis(1-ethoxyethoxy)-5-pentylbenzene
  参考文献：
  名称：

  ATPH促进的选择性IMDA反应的实验和计算研究：Δ9-THC的短总合成

  摘要：

  幸运的逆转：固有顺式分子内Diels-Alder反应的立体选择性是通过促进与铝，三（2,6- diphenylphenoxide）（ATPH）反转，使天然产物Δ的总合成9 -四氢大麻酚（参见方案）。计算研究预测了实验结果，并阐明了这些Diels-Alder反应中立体控制的影响。

  DOI：

  10.1002/chem.201001176

文献信息

• Synthesis of 5′-(2H3)-(−)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol methyl ester methyl ether
  作者：Marcus A. Tius、G.S.Kamali Kannangara

  DOI：10.1016/s0040-4020(01)85608-8

  日期：1992.1

  A synthesis of 5′-(2H3)-(−)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol methyl ester methyl ether (4) has been accomplished from α-bromoenone 10. The key steps are the stereocontrolled cyclobutane ring opening of the cuprate adduct 18 and the cyclization of the cyclohexenyl triflate 21 with excess iodotrimethylsilane to produce Δ9-cyclohexenyl triflate 22. An efficient, stereospecific synthesis of optically

  的5'的合成- （2 ħ 3） - （ - ） - 11-NOR -9-羧基- Δ 9 -四氢大麻酚甲酯甲基醚（4）已被从α-bromoenone完成10。的关键步骤是铜酸盐加成物的立体控制环丁烷环开口18和环己烯基三氟甲磺酸酯的环化21用过量的三甲基碘硅烷，以产生Δ 9环己烯基三氟甲磺酸酯22。还已经完成了光学活性的（-）-d11-nor-9-酮-六氢大麻酚（8）的高效立体定向合成。
• Halogenated cannabinoid synthesis
  作者：Marcus A. Tius、G.S.Kamali Kannangara、Michael A. Kerr、Krista J.S. Grace

  DOI：10.1016/s0040-4020(01)90158-9

  日期：1993.4

  A convenient synthesis of several tricyclic and bicyclic fluoro- and iodo analogs of cannabinoids has been reported. A new, mild methodology for the synthesis of vinyl fluorides from vinylstannanes has also been demonstrated. These C9 halo-functionalized cannabinoid analogs, along with (-) and (+)-DELTA9-THC carboxylic acids, were screened for anti-inflammatory activity in the mouse ear edema assay. It was interesting Lo find that both enantiomers of DELTA9-THC carboxylic acid were moderately active as anti-inflammatories. The bicyclic vinyl iodide (18C) also showed appreciable anti-inflammatory activity.
• Experimental and Computational Studies into an ATPH-Promoted exo-Selective IMDA Reaction: A Short Total Synthesis of Δ9-THC
  作者：Emma L. Pearson、Nicholas Kanizaj、Anthony C. Willis、Michael N. Paddon-Row、Michael S. Sherburn

  DOI：10.1002/chem.201001176

  日期：——

  of fortune: The inherent cis stereoselectivity of an intramolecular Diels–Alder reaction is reversed through promotion with aluminum tris(2,6‐diphenylphenoxide) (ATPH), allowing a total synthesis of the natural product Δ9‐tetrahydrocannabinol (see scheme). Computational studies predict the experimental findings and shed light on the stereocontrolling influences at play in these Diels–Alder reactions

  幸运的逆转：固有顺式分子内Diels-Alder反应的立体选择性是通过促进与铝，三（2,6- diphenylphenoxide）（ATPH）反转，使天然产物Δ的总合成9 -四氢大麻酚（参见方案）。计算研究预测了实验结果，并阐明了这些Diels-Alder反应中立体控制的影响。